Ammonium Chloride → Tetralin

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Bis(pyridine)iodonium tetrafluoroborate (65.8 mg, 0.177 mmol) was suspended in methylene chloride (3.4 mL), and the suspension was cooled to −78° C. in a dry ice/acetone bath. A methylene chloride (1.8 mL) solution of 1-(4-methoxyphenyl)-2-phenyl-1-(4-pivaloyloxyphenyl)-3-butene (4, 56.0 mg, 0.135 mmol) was added to the suspension, and also a tribromoborane diethyl ether complex (0.015 mL, 0.118 mmol) was added stepwise three times. Thereafter, the reactant was stirred at −78° C. for 1 hour, then a saturated aqueous ammonium chloride solution (5 mL) was added thereto to stop the reaction, and the reactant was cooled to room temperature and then extracted three times with diethyl ether (10 mL). An organic layer was collected and rinsed with a saturated aqueous sodium chloride solution (10 mL), followed by drying with anhydrous sodium sulfate and concentrating. The residue was purified by thin layer chromatography to obtain the title compound as a light yellow oily substance (51.6 mg, yield 71%).

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